Quirky First Date Questions You Need To Slip Into Your Conversation

First dates are incredibly awkward, but they can also be a lot of fun if you approach them in the right way.

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Sure, this is your chance to get to know a bit about the other person and see if there’s chemistry. However, there are more interesting things than what they do for work and when their last relationship was (both of which are important, of course). If you want to inject a bit of fun into the date, here are some questions to consider asking. They’ll either love your quirkiness or think you’re off your head. Either way, you’ll get a feel for whether this person is for you or not.

1. If you were a breakfast cereal, which one would you be?

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This one’s a real conversation starter. Are they a sensible bran flake or a wild and colourful fruity loop? Their answer might reveal more than you’d think. Plus, it’s a great way to segue into breakfast preferences. Who knows, you might end up planning a quirky breakfast date for round two!

2. What’s the weirdest thing you’ve ever eaten?

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Get ready for some potentially hilarious (or gross) stories with this one. From fried insects to exotic fruits, you’re bound to hear something interesting. Just maybe don’t ask this one right before the food arrives. You don’t want to put them off their meal, especially if they’re about to try escargot for the first time!

3. If you could have any superpower, what would it be and why?

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Classic question, endless possibilities. Flying, invisibility, or maybe something oddly specific like the ability to always find matching socks? Their choice might give you a peek into their personality. Bonus points if they come up with a creative way to use their power for good — or mischief!

4. What’s the most embarrassing song on your playlist?

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Time to fess up to those guilty pleasures! Everyone’s got at least one song they’re a bit ashamed of loving. Whether it’s cheesy pop or dad rock, this question can lead to some fun admissions. You might even bond over your shared love of the Spice Girls. Girl power!

5. If you were a character in a movie, what would your catchphrase be?

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This one lets their creativity shine. Will they go for something profound, funny, or totally random? Whatever it is, you’ll get a glimpse of their sense of humour. Who knows, you might end up with an inside joke for future dates. “To infinity and beyond” is already taken, though!

6. What’s the strangest dream you’ve ever had?

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Dreams are weird, and that’s what makes them fun to talk about. Flying pigs, teeth falling out, or showing up to work naked — the possibilities are endless. Just be prepared for some seriously bizarre stories. And hey, if they say they never remember their dreams, that’s interesting info too!

7. If you could instantly become an expert in one thing, what would it be?

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This question can reveal a lot about their interests and aspirations. Are they practical, choosing something like car mechanics, or more whimsical, opting for unicorn taming? Whatever they pick, it’ll definitely lead to an interesting discussion. Maybe you’ll even learn something new!

8. What’s the most useless talent you have?

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Everyone’s got a party trick that’s utterly pointless but kind of impressive. Can they lick their elbow? Recite the alphabet backwards? Or maybe they can make a clover shape with their tongue. This is your chance to see their silly side. Bonus points if they’re willing to demonstrate!

9. If you could have dinner with any historical figure, who would it be, and what would you eat?

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This one’s a two-for-one special! You’ll learn about their interests in history and their food preferences. Maybe they want to discuss philosophy over pizza with Plato, or share a burger with Shakespeare. It’s a great way to get the conversation flowing — and maybe plan your next meal together!

10. What’s the weirdest item you own, and why do you have it?

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We all have that one thing that makes visitors go, “huh?”. Maybe it’s a life-size cardboard cutout of Nicolas Cage, or a collection of rubber ducks. Whatever it is, there’s bound to be a good story behind it. This question might just reveal their quirky side — embrace it!